The DP is a fairly big advantage, alone it is perhaps not worth the incremental price difference, but that plus the extra 2' and other options may make it so. On the "respect" front, some might put 4 Winns ahead of Glastron for fit and finish, but at this age craft, it's more about the condition and prior care. Which fitment appeals to you most? Same quality and condition of gel, upholstery, electronics, hardware? If the '99 winny's fitment looks equal or better, then that suggests it is either higher quality to start, or it was better cared for, or both. What does your better half think?